ISOACTEOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H36O15
Molecular Weight	624.5871
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]4(O[C@H]1[C@H](O)[C@@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@@H]1O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O

InChI

InChIKey=FNMHEHXNBNCPCI-QEOJJFGVSA-N

InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H36O15
Molecular Weight	624.5871
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28441758 | https://www.ncbi.nlm.nih.gov/pubmed/28616865

Isoacteoside (2-(3′,4′-dihydroxyphenyl)ethyl 6-O-caffeoyl-3-O-(α-l-rhamnopyranosyl)-β-d-glucopyranoside), a phenylethanoid glycoside isomeric to acteoside, exists in various plants, such as Cistanches spp., Castilleja spp. and Plantago spp. It exerts wide range of pharmacological activity including anti-inflammatory and cytoprotective actions.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Toll-like receptor 4 6 Target ID: CHEMBL5255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28616865	Inhibitor 8297
Aldose reductase 44 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24288293	Inhibitor 8297	0.83 µM [IC50]
Xanthine dehydrogenase 32 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10630118	Inhibitor 8297	45.48 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammatory diseases 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28616865 https://www.ncbi.nlm.nih.gov/pubmed/25975581	Primary		Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28441758	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum.	2001 Aug	11534758
Inhibitory activities of acteoside, isoacteoside, and its structural constituents against protein glycation in vitro.	2013 Dec	28510849
Acteoside and Isoacteoside Protect Amyloid β Peptide Induced Cytotoxicity, Cognitive Deficit and Neurochemical Disturbances In Vitro and In Vivo.	2017 Apr 24	28441758
Acteoside and Acyl-Migrated Acteoside, Compounds in Chinese Kudingcha Tea, Inhibit α-Amylase In Vitro.	2017 Jun	28486011
Isoacteoside, a dihydroxyphenylethyl glycoside, exhibits anti-inflammatory effects through blocking toll-like receptor 4 dimerization.	2017 Sep	28616865

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 2.5 or 5.0 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Isoacteoside inhibited D-GalN-induced death of hepatocytes (IC50-5.3 microM) and reduced TNF-alpha-induced cytotoxicity in L929 cells (IC50-22.7 microM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:38:02 GMT 2023` Edited by `admin` on `Fri Dec 15 20:38:02 GMT 2023`
Record UNII	588LJK42AP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOACTEOSIDE

Common Name

English

ISOVERBASCOSIDE

Common Name

English

NSC-729649

Code

English

.BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 6-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)

Systematic Name

English

Code System Code Type Description

CAS

61303-13-7